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F.i.s. Fabbrica Italiana Sintetici S.p.a.

Giancarlo Arvotti

Andrea Castellin

Riccardo Motterle

Stefano Fogal

Elisabetta Bergantino

Marco Galvagni

The present invention relates to the stereoselective synthesis of (4aS,7aS)-octahydro-1H-pyrrolo[3,4-b]pyridine, as well as the conversion thereof, to give Moxifloxacin. Particularly, the present invention relates to a method for the synthesis of (4aS,7aS)-octahydro-1H-pyrrolo[3,4-b]pyridine of formula (I) comprising: (a) the optical resolution by enzymatic hydrolysis of the intermediate dialkyl-1-alkylcarbonylpiperidine-2,3-dicarboxylate racemate of formula (II) to give, following isolation, the intermediate dialkyl-(2S,3R)-1-alkylcarbonyl-piperidine-2,3-dicarboxylate of formula (III) in which AIk is a straight or branched C1-C5 alkyl group; (b) the conversion of the intermediate (III) to (4aR,7aS)-1-alkylcarbonylhexahydrofuro[3,4-b]pyridine-5,7-dione of formula (IV) in which AIk has the meanings set forth above; (c) the conversion of the intermediate (IV) to (4aS,7as)-octahydro-1H-pyrrolo[3,4-b]pyridine of formula (I) with an optical purity above 99%. 

Synthesis of (4aS,7aS)-octahydro-1H-pyrrolo[3,4-b]pyridine

The present invention relates to an industrial process for the reduction of 4-androstene-3,17-dione in order to obtain testosterone using a particularly stable and selective enzyme produced in a recombinant manner.

Process for the preparation of testosterone

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Vicenza, Italy

Giancarlo Arvotti